


Professor Dean Winchester

by ShipperOfTheShips



Category: Supernatural
Genre: AU, Alternate Universe, Classroom Fantasizing, Crowley and Cas are fuck buddies, Dean teaches English, Destiel - Freeform, Fantasizing, Highschool AU, Kevin Tran is an anatomy teacher, M/M, Professor!Dean, Sam teaches Social Studies, Student!Cas
Language: English
Status: In-Progress
Published: 2016-01-04
Updated: 2016-04-02
Packaged: 2018-05-11 19:17:54
Rating: Explicit
Warnings: Underage
Chapters: 4
Words: 2,802
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5638750
Author URL: https://archiveofourown.org/users/ShipperOfTheShips/pseuds/ShipperOfTheShips
Summary: <blockquote class="userstuff">
              <p>Cas knows he shouldn't be messing around with his grades, but he just knew Professor Winchester would keep him after class to scold him for not doing his best.</p>
            </blockquote>





	1. The Scolding

  
"Castiel, I know you can do better than this; I've seen it for myself," Professor Winchester scolds, slamming Cas Novak's C+ essay on the desktop before him.   
  


"You are a fantastic writer, and I don't understand why you would lower yourself below your true potential."   
  


Castiel tries to listen, he really does, but Professor Dean Winchester is making it incredibly difficult. He has loosened his tie, removed his usual black suit jacket, and paces in front of him. Castiel watches Dean's arms as he chastises his student for handing in a subpar paper. All Cas can focus on is the rumble of his teacher's gruff voice and the way the white dress shirt stretches across his broad, muscular chest.   
  


"Are you even paying attention?" Professor Winchester demands, coming to a halt.   
  


"Uh--yeah--er yessir," Castiel answers, hastily wiping the drop of drool from the corner of her mouth. "And I do apologise for less than my best work on this paper. I won't let it happen again."   
  


The professor sighs, Castiel subtly adjusts his ever tightening jeans as Dean's breath washes over him. Cas knows that, as soon as he gets home, he'll be stripping down and rubbing a quick one out before supper. Just to tide him over until he can get a decent amount of alone time.   
  


"You just have so much potential and I don't want to see that go to waste," Dean says kindly.   
  


"Now," he leans away, not noticing Cas's strangled sigh, "I won't keep you any longer. Have a great weekend Castiel."   
  


"Thank you, sir. Have a nice weekend."   
  


Castiel gathers his backpack and begins his walk home with a raging hard on.


	2. Fantasy

**Summary for the Chapter:**

> Castiel has some alone time.

Castiel lets out a soft sigh as Dean presses a thick middle finger against his quivering hole, gaining entrance easily. The older man gives a quiet chuckle, sliding the digit in to the second knuckle.

"Like that, do ya?"

"Yes," Cas whispers.

"Yes what?" Dean demands.

"Yes, sir," he amends and is rewarded with a second finger slipping in alongside the first. A low moan reverberates in his throat.

Dean hovers over his writhing student as he scissors his fingers, stretching the warm, tight hole he will soon be fucking. He adds the third and and final digit, groaning as the already tight muscles squeeze his thrusting fingers. Cas whimpers as the fingers are removed but shivers with anticipation when they are immediately replaced with the head of the dick he's been fantasising about for the past two and a half years.

"Are you ready, Castiel?" Dean asks quietly, sucking softly just under Cas's earlobe.

"Yes, sir. Please," Cas pants. "I'm ready."

With a sharp grunt, Dean jerks his hips forward, slamming his entire length into the beautiful teen beneath him. Cas tilts his head to allow his professor to lick, suck, and bite along the side of his neck. He relishes the feel of Dean's stubble scratching against his soft skin.

If the teeth and stubble aren't enough to get Cas to the edge, then the calloused fingertips brushing over his sensitive nipples coupled with the throbbing cock currently thrusting into him would do the trick. Soon.  
He lifts his hips to meet every thrust, loving the filthy sounds pouring from the gorgeous mouth of the man above him.

"Please, sir," Cas gasps suddenly. "I'm so close. Can I come? Please?"

"If I weren't so close myself, I would say no." Dean's thrusts have become harder, losing their rhythm.

"Please," Cas begs.

Dean leans down to whisper against his student's ear. "Come for me, Castiel."

Cas releases with a strangled groan, his hips stuttering and Dean's body spasming against him.

There is a sudden, loud banging on his bedroom door and Castiel is suddenly, once again, alone in his bed.

"Soup's on, little bro," Gabriel hollers.

"I'll be down in a bit," Cas yells back. He listens to Gabriel stomp back down the stairs.

"Fuck," he sighs, slumping against the mattress behind him.

**Notes for the Chapter:**

> Once again, I apologize for a short as all get out chapter.  
> Leave me some requests for future chapters and I'll do my best to make them happen!!  
> ~C


	3. The Real Deal

**Summary for the Chapter:**

> Cas finally gets what he wants.

**Notes for the Chapter:**

> I am so sorry that I didn't get to post this Tuesday evening. I'd been suckered into babysitting my (almost) 2 year old nephew and he makes getting any work done rather difficult.  
> Anyways, I hope you enjoy this chapter!!  
> ~C

The next morning in class, Castiel can focus even less than normal on anything Professor Winchester is talking about. The only thing at the forefront of his mind is the thought of Winchester bending him over the big oak desk at the front of the room, and making him forget his own name.

  
So badly does he want to feel that polished wood digging into his skin, Cas only just notices the oddly quiet of the room. He glances around and sees that professor has stopped speaking and is now staring intently at him, causing the same of the rest of the room.

  
"Now that Mr. Novak has decided to rejoin us," he says, never taking his eyes off the boy in question, "I was showing the class the well placed symbols in the chapter thus far."

  
He has no idea if Dean had noticed what Cas was thinking about. He is having a hard time believing he was making any type of face, because honestly, he's a seasoned pro at fantasizing the filthiest fantasies, with a completely neutral expression, in public. He has had at least four years of practice throughout his schoolin career.

  
For instance, there had been the time in seventh grade when he'd imagined Crowley, the boy who had been (and is currently) his science lab partner, let Cas suck him off under the table. Later on a year later, he came in his pants just thinking about what would happen if he went into the football team's locker room completely naked. The possibilities for that were endless, and he hadn't been able to control himself any longer. Most of those boys are now playing football for their high school and Cas still thinks of that from time to time. He thinks that Lucifer, their quarterback, would take him first and then pass him down the line.

  
_Jesus Christ,_ he thinks, _I'm way off subject._

  
How the hell could Winchester notice this? Unless he's been paying closer attention to Castiel than he thinks. Somehow, he doesn't think that's a possibility, being that he is merely a student and Dean is an amazingly attractive teacher who only wants to see his pupils to pass with flying colors.

  
He mindlessly goes through the assignment, completing it within minutes. Afterwards, he sits, hands in his hair fighting the beginnings of a panic attack. Does Dean know that Castiel has been fantasizing about him during class? Will he be confronted? If he is, will he boldly offer himself, or will he shamefully apologize and never look him in the eye again?

  
He would have to drop this class and gawk at the gorgeous professor from afar -- secretly.

  
Crap.

  
"Everything all right, Mr. Novak?"

  
Cas startles and looks up to the professor, trying not to allow his eyes to linger at any one place for too long. He succeeds. Mostly.

  
"Uhm, yes sir. Just didn't get much sleep."

  
"And, because of this you can't concentrate?" Dean asks. He glances around, as if making sure no one is listening. Cas peers at his classmates as well, wondering if he was the only one noticing how odd Winchester is acting. "Because, you can sit in my office if you need to. It's quieter." Cas shivers slightly when Dean rests a heavy hand on his shoulder, squeezing slightly. He nearly misses the smug half-grin as the educator begins to turn away, motioning for Cas to follow him toward the small office.

  
"Thank you, sir," Cas mutters. "I'll try to finish quickly."

  
"I'm sure,” Winchester mutters.

  
"What?"

  
"Here ya go." Dean opens the door, ushering Cas into the room. "You can stay as long as you need." Dean winks as he shuts the door behind himself.

“What in the actual hell is going on?” Cas mutters quietly as he looks around the office. He chooses to take a seat in the big comfy-looking chair to take a closer look at the small picture framed at the corner of the desk. He can't help but grin back at the photo of Professor Winchester and his brother, also a teacher at the school, each holding up a large catfish proudly for the camera.

Cas shakes his head as he paces around the desk, looking at anything personal adorning the shelves and tabletops. The pictures of Dean and his brother, little trinkets, and well-read books. As he is making his second lap around the office, the last bell sounds causing him to jump and knock a cup of pencils onto the floor.

Castiel is on his hands and knees, ass high in the air, when he hears the door being opened behind him. Startled, Cas bangs his head as he tries to stand, ending up facing the professor while still sitting on his knees. At the almost hungry look on Dean’s face, Cas’s breath catches in his throat, his eyes landing on the teacher's crotch.

“Damn,” Dean breathes, taking in the sight before him, “I know you’ve been eye fucking me for a while now, but I was still thinking I'd have to talk you into it.”

Cas’s eyebrows seem to jump into his hairline. He feels the urge to pinch himself, just to make sure he isn't dreaming. But as Dean reaches for his belt, Cas feels his own pants begin to tighten. Specifically in the crotch area. The teacher steps forward, brandishing his hardening cock.

“Whaddya say, Castiel?” he asks, coming a step closer. Cas wets his lips, accidentally brushing the tip of his tongue against head of Dean’s dick, making him groan.

Without answering, Cas leans forward, wrapping his lips around the tip of Dean’s cock, sucking gently before taking him in completely. He relaxes his throat and pulls Dean closer by the hips, not stopping until his nose is flush against the professor’s pubic bone. Dean lets out a groan and fists a hand in the boy's dark hair.

“Fuck,” he sighs. “You're so good, baby.”

Castiel looks up at Dean as he bobs up and down, slurping and sucking on the stiff cock until his teacher takes the hint and holds a hand on either side of his head and begins to thrust into the waiting mouth. The teen moans around the dick that has starred in so many of his “alone time” thoughts. He's wanted this so badly, he knows he will come untouched, soiling his pants, but it's worth it. He doesn't even care anymore if he's imagining it, just as long as he can think back on it later this evening when he'll be hard again. He never knew how much he would enjoy to have Dean Winchester call him baby, but that is definitely going to happen more often in his fantasies from here on out.

Gently, Cas massages Dean’s balls with his fingertips, earning an appreciative sigh and a tug on his hair. Castiel’s dick jumps at the sharp pull of his hair. _Damn,_ he thinks, _You learn something new every day._ He had no idea he would like to have his hair pulled, or being called baby in that deep, rough voice. He sucks harder, moaning like a two bit whore the entire time, knowing what he was doing to his teacher. Dean pulls Cas’s hair as he pulls the boy on and off of his throbbing cock.

“Oh fuck, Cas,” Dean pants, thrusting harder into Castiel’s throat. “I'm gonna come.”

Cas groans around Dean as he feels himself reaching the point of no return. He grips the teacher’s hips as an orgasm rips through his body, forcing his eyes closed and a low moan to vibrate in his throat. Dean fists his hands into Castiel’s hair as he gives one last thrust, spilling his seed into his student's mouth with a shout. Cas continues to suck gently until Dean pulls back, allowing his softening cock to slip from the boy's lips.

“If I'd have known,” says Cas, his voice hoarse, “I would've been naked and waiting on your desk.”

Dean laughs and pulls Castiel to his feet before tilting his chin up with his fingertips. He presses his lips to those that were just wrapped around his cock, thoroughly enjoying the taste of himself mixed with the taste of Castiel. Cas accepts the probing tongue into his mouth as he feels Dean’s hands begin their journey to Castiel’s spent prick. He stops them at his belt.

“Do you not want--?”

“I, uh--when you--”

“On my god,” Dean groans, pulling Cas back to him, kissing him harder this time, more desperate. “You have no idea how hot that is.”

**Notes for the Chapter:**

> Also, I'm sorry for the weird paragraph spacing idk what happened there and I don't know how to fix it and it is 3:45am right now, so I'm going to bed.  
> Goodnight people!!  
> ~C


	4. The Sports Shed

**Summary for the Chapter:**

> Castiel is frustrated and needs a friend.

**Notes for the Chapter:**

> I'm sorry it's been so long. I was having a bit (a lot) of writer's block and I couldn't think of anything.  
> ~C

It's Tuesday morning and Castiel isn’t 100% on whether the previous day was a dream or not. Without knowing for sure, he decides to avoid Dean Winchester for as long as he can. But just because he can avoid him physically, doesn't mean he can avoid him mentally.

By third period, he's rock hard and in desperate need of release.

“Hello, Castiel,” Crowley says as his lab partner approaches. “You seem agitated.”

Cas glowers and turns to face the front of the room. Crowley snorts when Cas tries, and fails, to cover himself discreetly.

“Anything I can lend a hand to?” he asks, shifting his eyes to Cas’s crotch and back up again. Castiel tilts his head, eyeing the other boy. He would love a helping hand. Better yet, he would rather enjoy another helping body part.

“Come with me to the shed after class?”

Crowley agrees with a grin as the bell sounds and the boys turn their focus to Professor Tran (the boy genius) as he begins to explain the finer workings of the heart.

 

  
Fifty excruciatingly long minutes later, Castiel leads the way through the back doors of the school and across the football field to the small storage building that houses all the sports equipment. Crowley pulls the door closed as Cas clears the table of boxes of rackets and tennis balls with an annoyed huff.

“We've got thirty minutes,” Crowley informs him as he pushes Cas against the table, palming him through his jeans. “You want me to suck or fuck?”

“Fuck.”

“Right then. Drop ‘em and turn around.”

Cas quickly rids himself of his blue jeans and boxershorts before turning to bend over the white plastic table. Crowley steps up behind him, pulling his cheeks apart and slipping a spit-slick finger inside of the other teen. A desperate sigh spills from Castiel as he pushes back against his friend’s hand.

“We don't have time for slow,” Cas complains. “Hurry up.”

Crowley grumbles about not fully appreciating the sensations, but complies. He shoves in another finger for a few thrusts before yanking them both out and lining himself up to the waiting hole before him. Crowley pulls a silver packet of lube from his pocket, tearing it open spreading the clear liquid over himself before pressing the head of his dick to Castiel’s quivering entrance. Gripping Cas’s hips, Crowley thrusts into him; just the tip at first, but with several quick pumps, he’s buried to the hilt.

Cas pushes back against Crowley, silently begging him to move. If they weren't pressed for time, Cas knows that his jackass friend would make him beg out loud. He’d never minded it before, it was more of a turn on than anything, but he hated when Crowley tried to tell him what to do.

“Fuck,” Castiel sighs, enjoying the feel of the cock thrusting into him as Crowley leans over him, nipping at his ear. He tilts his head back, encouraging the other boy to continue down his neck.

A hands wraps around Castiel’s aching cock, forcing a strangled moan from his throat. After a few strokes, Cas knows he won't last much longer. He's been hard for far too long already, and he feels if he doesn't come soon, he’ll explode.

“Oh, _fuck_. Don't stop,” he pleads.

“That's it, angel,” Crowley mutters as Cas pushes back onto Crowley’s prick while simultaneously thrusting into his hand.

“ _Fuck_.” Cas grunts, his knuckles white as he grips the table edges, spilling his load onto the ground. Crowley gives two final pumps before letting go inside of the other boy. Outside, the bell rings, signaling the end of lunch time.

The boys clean themselves (with a roll of paper towels they'd stashed on a shelf for such purposes) before redressing and heading back to the main building.

“Thank you,” Cas says, offering Crowley a brown paper bag. “I needed that.”

“Anytime,” Crowley answers lightly. “What's this?”

“Since you missed lunch ‘cause of me, I figured I'd share mine.”

“It's not like fucking you is a chore,” he chuckles. “But hey, free food. Thanks.”

Castiel rolls his eyes as he leads the way into their next class: Social Studies, taught by none other than Professor Sam Winchester. 

**Notes for the Chapter:**

> If you have any suggestions or ideas, as always, leave a comment!  
> ~C

**Author's Note:**

> I know this is super short, but I'll be adding on to it possibly later on today or tomorrow with Castiel's bedtime fantasy ;)  
> ~C


End file.
